U.S. District Judge Paul Engelmayer in Manhattan agreed with bond trustee Bank of New York Mellon Corp that holders of Chesapeake's 6.775 notes maturing in 2019 were entitled to a special "make-whole" price because of the early redemption.

The payout is more than triple the roughly $100 million that Chesapeake hoped to distribute in "restitutionary" damages.

It originally argued that its March 15, 2013 redemption notice entitled it to redeem the notes at face value, but a federal appeals court in November said that notice came one month late.

Bank of New York Mellon acted on behalf of a variety of hedge funds and other bondholders such as Ares Management LLC, Aurelius Capital Management LP, P. Schoenfeld Asset Management LP and Taconic Capital Advisors LP.

Chesapeake spokesman Gordon Pennoyer declined to comment. Bank of New York Mellon had no immediate comment.

In afternoon trading, Chesapeake shares were down 16 cents at $11.52.

The redemption was intended to help Chesapeake reduce a debt burden that the Oklahoma City-based company had accumulated under former Chief Executive Aubrey McClendon, and offset natural gas prices that had fallen to a decade low.

But Engelmayer, whose original ruling in Chesapeake's favor was reversed by the appeals court, said investors were entitled to hold Chesapeake to its obligations under the bond indenture, rather than accept lesser sums.

"Investors who decided to buy (or hold) the 2019 notes were beneficiaries of a contract," he wrote. "The interest in respecting investors' legitimate expectations therefore supports a payout keyed to the indenture's treatment of redemptions after March 15, 2013."

The notes were redeemed in May 2013 as part of a refinancing, and Chesapeake recorded a $33 million loss at the time.

The case is Chesapeake Energy Corp v. Bank of New York Mellon Trust Co, U.S. District Court, Southern District of New York, No. 13-01582.

(Reporting by Jonathan Stempel in New York; Editing by Phil Berlowitz)

By Jonathan Stempel